Winsted, CT Homes

• 

  $379,000 Sold May 09, 2025

  • 1,531 Sq Ft
  • $248/SF
  • 90 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  244 Colebrook Rd, Winsted, CT 06098

  Welcome to 244 Colebrook Road, a beautifully renovated home that perfectly blends modern upgrades with timeless charm. Move-in ready, this home features thoughtful updates designed to suit all your lifestyle needs. Virtually staged. The first floor opens to a formal living room that seamlessly connects to a gourmet kitchen, outfitted with all-new appliances and a large quartz island seating

  Carol York For Sale By Owner Connecticut

  244 Colebrook Rd, Winsted, CT 06098
• 

  Est $1,079,015 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,963 Sq Ft

  411 W Wakefield Blvd, Winsted, CT 06098

  411 W Wakefield Blvd, Winsted, CT 06098
• 

  

  

  /27

  $388,000

  • 5 Beds
  • 2 Baths
  • 2,403 Sq Ft

  409 N Main St, Winsted, CT 06098

  This versatile 2-family home would make a perfect owner occupant first floor unit with 3 bedrooms, with a 2 bedroom second floor apartment. Private entrances with separate utilities. Let your rental income help pay your mortgage. Each unit comes with formal living and dining rooms. Refinished original wide pine flooring. Large main Kitchen with lots of cabinet space which walks out to a

  Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  $160,000 Sold May 07, 2025

  • 992 Sq Ft
  • $161/SF
  • 37 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  37 Riveredge Dr Unit 37, Winsted, CT 06098

  Enjoy the private and peaceful setting of Still River right from your bedroom window or private patio all the while being close to the many amenities offered in town. Inside this well-maintained condo you'll find an abundance of natural light flowing in every room, a bright slider opening up to your own patio, all new paint throughout, lots of storage and durable like-new flooring on the main and

  Erin Ruwet Century 21 AllPoints Realty

  37 Riveredge Dr Unit 37, Winsted, CT 06098
• 

  Est $284,700 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
• 

  

  /24

  $229,900

  • 5 Beds
  • 1.5 Baths
  • 2,310 Sq Ft

  30 Mountain Ave, Winsted, CT 06098

  Not afraid of some peeling paint or rotting wood? This is the house for you! 30 Mountain Ave with 5 beds, 1.5 baths is your opportunity to bring a vision to life. Located in a welcoming neighborhood, it offers a generous layout ready for customization and renovation. Whether you're a seasoned investor or a first-time buyer with a knack for design, this home has the bones to become something

  Derek Greene Derek Greene

  30 Mountain Ave, Winsted, CT 06098
• 

  $269,000 Sold May 05, 2025

  • 1,175 Sq Ft
  • $229/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1880

  39 Finn St, Winsted, CT 06098

  Fabulous Opportunity to own in the Highland lake community. Walking distance to both beaches and boat launch. This adorable3-4 bedroom home has new hardwood floors thru out the first floor, has been freshly painted, new fridge and stove, roof only 2 yrs old, thermal paned windows. Large storage shed. Open concept with a living room/dining room combo. Large area for gardening and ready to move

  Christine Hunter Hunter Real Estate, LLC

  39 Finn St, Winsted, CT 06098
• 

  Est $638,770 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  715 W Wakefield Blvd, Winsted, CT 06098

  715 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /30

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,287 Sq Ft

  50 Manchester Heights, Winsted, CT 06098

  Charming Country Cape with Cottagecore appeal on just over an acre of land and situated on a culd-de-sac. Located off the beaten path in the quiet hills of Winchester, this storybook Cape-style home offers the perfect blend of rustic charm and modern comfort. Convenient to Route 8 and just minutes to town amenities. Enjoy the natural beauty surrounding the property while relaxing on the deck and

  Lisa Bredice William Raveis Real Estate

  50 Manchester Heights, Winsted, CT 06098
• 

  $70,000 Sold May 01, 2025

  • 2,016 Sq Ft
  • $35/SF
  • 18 Days On Market

  • 5 Beds
  • Built 1800

  50-52 Cottage St, Winchester, CT 06098

  Investor Special! This four-level, two-family property at 50-52 Cottage St. was previously prepared for demolition but may still hold potential for the right investor. A complete rehab or possible teardown, this property is being sold as-is and will require vision, expertise, and cash-no financing will qualify. Whether you're looking for a full-scale renovation project or a lot for future

  David Sartirana Northwest CT Realty

  50-52 Cottage St, Winchester, CT 06098
• 

  Est $265,260 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
• 

  

  /34

  $319,900

  • 4 Beds
  • 1 Bath
  • 1,849 Sq Ft

  284 Gilbert Ave, Winsted, CT 06098

  Welcome to 284 Gilbert Avenue-a charming 4-bedroom Cape that combines efficient updates with inviting living spaces. Approximately 1,849 sq ft of sun-splashed interiors begin with a spacious eat-in kitchen featuring generous cabinetry, a dining area, and sliders that open to an elevated deck-perfect for grilling while enjoying the privacy of the beautifully manicured backyard. The main level also

  David Sartirana Northwest CT Realty

  284 Gilbert Ave, Winsted, CT 06098
• 

  $679,000 Sold Apr 30, 2025

  • 3,870 Sq Ft
  • $175/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  110 South Rd, Winsted, CT 06098

  Discover your private sanctuary in the heart of historic Winchester Center, where tranquility meets nature! This contemporary Cape-style home boasts spacious, light-filled rooms that have been thoughtfully updated throughout. Elegant details such as crown molding, beams, skylights & oversized windows invite the beauty of the outdoors in-all showcasing your private pond! The main floor is designed

  Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
• 

  Est $158,958 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
• 

  

  /18

  $249,000

  • 2 Beds
  • 1 Bath
  • 674 Sq Ft

  343 W Wakefield Blvd, Winsted, CT 06098

  Your oasis awaits!!! Schedule your appointment today and come view this adorable Bungalow. There is so much potential to be made here. Bring your ideas and creativity as the seller is motivated, bring all offers!!!

  Patrick Precourt Dorrance Realty

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  $160,000 Sold Apr 29, 2025

  • 992 Sq Ft
  • $161/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  Come see this wonderful sought after condo in a great neighborhood that has been freshly painted and all new appliances in the kitchen as well as a newer water heater that is just a few years old. Close proximity to town and route 8 and just down the street from the Northwestern Connecticut Community College. This unit has a garage that is directly across from the condo and has an additional

  Maria Smith Turning Point Realty, LLC

  14 Riveredge Dr Unit 14, Winsted, CT 06098
• 

  Est $251,737 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,010 Sq Ft

  22 Stanton Ave, Winsted, CT 06098

  22 Stanton Ave, Winsted, CT 06098
• 

  

  /40

  $1,595,000

  • 5 Beds
  • 2 Baths
  • 3,693 Sq Ft

  424 E Wakefield Blvd, Winsted, CT 06098

  Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

  KAREN NEWTON William Pitt Sotheby's Int'l

  424 E Wakefield Blvd, Winsted, CT 06098
• 

  $90,000 Sold Apr 25, 2025

  • 936 Sq Ft
  • $96/SF
  • 18 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1935

  109 Marshall St, Winsted, CT 06098

  Charming bungalow with great potential! This 936 sq. ft. home features 6 rooms, including 3 bedrooms and 1 full bath, situated on a spacious 0.80-acre lot. A detached one-car garage provides additional storage or parking. While this home is in poor condition and will require significant renovation, it presents an excellent opportunity for investors or buyers looking to restore and customize. Will

  David Sartirana Northwest CT Realty

  109 Marshall St, Winsted, CT 06098
• 

  Est $583,976 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  319 Taylor Brook Rd, Winsted, CT 06098

  319 Taylor Brook Rd, Winsted, CT 06098
• 

  

  /4

  $50,000

  • Land
  • 0.41 Acre
  • $121,951 per Acre

  130 Alpha Ave, Winsted, CT 06098

  Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

  Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, Winsted, CT 06098
• 

  $410,000 Sold Apr 24, 2025

  • 2,313 Sq Ft
  • $177/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1971

  52 Lakeview Rd, Winsted, CT 06098

  Welcome to 52 Lakeview Rd, a meticulously maintained Colonial home that has been lovingly cared for by the same family for over 50 years. This 2,300 sq. ft. residence is set on a spacious .47-acre lot in a peaceful, rural neighborhood, offering both privacy and convenience. The main level features a well-designed layout, including a formal living room and dining room, perfect for entertaining.

  David Sartirana Northwest CT Realty

  52 Lakeview Rd, Winsted, CT 06098
• 

  Est $263,255 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,654 Sq Ft

  220 Walnut St, Winsted, CT 06098

  220 Walnut St, Winsted, CT 06098
• 

  

  /21

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  150 Mathew Rd, Winsted, CT 06098

  Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. 6,500 watt whole house generator. 8x12 shed with power, 35 Amp out side outlet for camper, working chimney for wood stove on lower level, ASSUMABLE MORTGAGE!

  Josh Dionne Commercial Services Realty

  150 Mathew Rd, Winsted, CT 06098
• 

  $220,000 Sold Apr 24, 2025

  • 3,115 Sq Ft
  • $71/SF
  • 14 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1900

  830 Main St, Winsted, CT 06098

  Large side by side duplex with 1 and half baths on each side and a finished attic on each side. Lots of potential here but freeze damage as well. As is sale or repairs possible.

  Michelle Grant Coldwell Banker Premier Real Estate

  830 Main St, Winsted, CT 06098
• 

  Est $258,057 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  39 Rockwell St, Winsted, CT 06098

  39 Rockwell St, Winsted, CT 06098
• 

  

  /3

  $225,000

  • Land
  • 0.23 Acre
  • $978,261 per Acre

  129 Shore Dr, Winsted, CT 06098

  A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

  Annie Simard LPT Realty

  129 Shore Dr, Winsted, CT 06098
• 

  $275,000 Sold Apr 23, 2025

  • 2,191 Sq Ft
  • $126/SF
  • 41 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1880

  151 Elm St, Winsted, CT 06098

  Step into the warmth and character of this beautiful 5-bedroom single-family home, ideally located in the heart of Winsted. With a wrap-around front porch and a screened rear porch, this home offers the perfect blend of classic charm and modern convenience. Inside, you'll find hardwood floors throughout most of the house, a full bay window in the living room that fills the space with natural

  Jeffrey Liskin Northwest CT Realty

  151 Elm St, Winsted, CT 06098
• 

  Est $835,003 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  206 E Wakefield Blvd, Winsted, CT 06098

  206 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /19

  $230,000

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  39 Orchard St, Winsted, CT 06098

  Back on the market, buyer's financing fell through. Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends classic charm with modern conveniences, featuring a spacious layout, abundant natural light, and stylish updates throughout. The inviting living room offers a cozy atmosphere perfect for gatherings. The updated kitchen boasts

  Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
• 

  $289,900 Sold Apr 21, 2025

  • 988 Sq Ft
  • $293/SF
  • 61 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  315 E Wakefield Blvd, Winsted, CT 06098

  Charming ranch style home with year round water views! This beautifully updated 3-bedroom, 1-bath ranch home in the sought-after Highland Lake community in Winsted is a true gem. The home has been meticulously cared for, blending modern updates with classic charm. Inside, you'll find a cozy, well-maintained living space that feels inviting and comfortable. The property boasts a spacious, full

  Heather Crabtree Coldwell Banker Realty

  315 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $338,263 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft

  144 Meadow St, Winsted, CT 06098

  144 Meadow St, Winsted, CT 06098
• 

  

  /4

  $14,999

  • Land
  • 0.12 Acre
  • $124,992 per Acre

  320 White Oak Trail, Winchester, CT 06098

  Plot Of Land Valued at $32,060 Property ID #: 033 105C 044+45 Zoning: HL

  Dillon Cass eRealty Advisors, Inc.

  320 White Oak Trail, Winchester, CT 06098
• 

  $290,000 Sold Apr 21, 2025

  • 2,338 Sq Ft
  • $124/SF
  • 6 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1886

  18 Upland Rd, Winsted, CT 06098

  A Great Investment opportunity in this classic charming multi two unit home. The location is convenient to many amenities including Dining, Community College, Highland Lake recreation and much more. Each unit has Washer & Dryer hookups. Up grades include New High Gas Efficiency Furnaces and Hot Water Heaters in 2020. New Thermal Windows & Blown In Insulation 2021 & 2022. Two Car Garage, Large

  Linda Ganem Borla & Associates Real Estate

  18 Upland Rd, Winsted, CT 06098
• 

  Est $202,799 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 30, Winsted, CT 06098

  111 Riverton Rd Unit 30, Winsted, CT 06098
• 

  

  /36

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
• 

  $275,000 Sold Apr 17, 2025

  • 1,287 Sq Ft
  • $214/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1948

  58 Cherry St, Winsted, CT 06098

  Charming Cape Cod retreat just a short stroll from the beautiful beaches of Highland Lake! This well-maintained 3-bedroom, 2-bath home has been a cherished getaway for years, offering the perfect blend of comfort and convenience. The main level features a sun-filled living room, a dining room ideal for gatherings, and a kitchen with a center island for easy meal prep. A cozy bedroom and a full

  David Sartirana Northwest CT Realty

  58 Cherry St, Winsted, CT 06098
• 

  Est $268,445 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, Winsted, CT 06098
• 

  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  David Sartirana Northwest CT Realty

  99 Hubbard St, Winsted, CT 06098
• 

  $275,000 Sold Apr 16, 2025

  • 1,277 Sq Ft
  • $215/SF
  • 114 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  493 N Main St, Winsted, CT 06098

  Highest and best by 3/10 at 6 PM. Back on the market! Enjoy living in your own home nestled in the scenic Litchfield Hills in this newly renovated three-bedroom house with many updates: Refrigerator, range, microwave, dishwasher, and first floor washer/dryer less than a year old. Hot water heater 2023. Updated electrical 2024. Furnace serviced and updated with new burner 2024. 3 new exterior

  Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098

Showing Results 41 - 80, Page 2 of 18